methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

Base Information

Chemical Name:methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate
CAS No.:1197026-61-1
Molecular Formula:C₂₁H₃₂BNO₇
Molecular Weight:421.299
Hs Code.:

Synonyms:methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

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Chemical Property of methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

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Technology Process of methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

There total 6 articles about methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 218912-19-7
N-(tert-butyloxycarbonyl)-D-(3-iodo-4-methoxyphenyl)glycine methyl ester

: 1197026-61-1
methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

Guidance literature:: With 2-(dicyclohexylphosphino)biphenyl; Pd(CH₃CO₂)2; triethylamine; In 1,4-dioxane; Pd(CH3CO2)2 and N(CH2CH3)3 added to soln. of ligand and 2-(dicyclohexylphosphino)biphenyl in 1,4-dioxane, degassed, B-compound added over 15 min, heated to 85°C for 30 min, aq. soln. of NH4Cl added; extd. with ethyl acetate, purified either column chromy. with cyclohexane-EtOAc 9:1-3:7 or by crystn. from cyclohexane; elem. anal.;
DOI:10.1039/c2ob25373a

Reference yield: 33.0%

: 73183-34-3
bis(pinacol)diborane

: 192328-47-5
methyl (R)-N-(tert-butoxycarbonyl)-2-(3-bromo-4-methoxyphenyl)glycinate

: 1197026-61-1
methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 22h; Inert atmosphere;
DOI:10.1021/jo901899w

Reference yield:

: 22818-40-2
D-4-hydroxyphenylglycine

: 1197026-61-1
methyl (-)-(2R)-tert-butyloxycarbonylamino-[4-methoxy-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]acetate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydroxide / 1,3-dioxane; water / 4 h / 20 °C

2: potassium carbonate / acetone / 16 h / 50 °C

3: iodine; silver trifluoroacetate / chloroform / 15 h / 20 °C

4: palladium diacetate; triethylamine; CyJohnPhos / 1,4-dioxane / 0.75 h / 85 °C

With iodine; palladium diacetate; silver trifluoroacetate; potassium carbonate; triethylamine; sodium hydroxide; CyJohnPhos; In 1,3-dioxane; 1,4-dioxane; chloroform; water; acetone;
DOI:10.1039/c2ob25373a